One-pot two-component [3 + 2] cycloaddition/annulation protocol for the synthesis of highly functionalized thiophene derivatives

Journal of Organic Chemistry

Volumn 76, Issue 19, 2011, Pages 8009-8014

  Nandi, Ganesh Chandra ^a   Samai, Subhasis ^a   Singh, Maya Shankar ^a  

^a BANARAS HINDU UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

4-DIMETHYLAMINOPYRIDINE; FERROCENYL GROUPS; FUNCTIONALIZED; HIGH YIELD; ONE POT; ROOM TEMPERATURE; THIOPHENE DERIVATIVES; TWO-COMPONENT;

THIOPHENE;

SYNTHESIS (CHEMICAL);

4 DIMETHYLAMINOPYRIDINE; BETA KETODITHIOESTER; CARBOXYLIC ACID DERIVATIVE; DIALKYL ACETYLENEDICARBOXYLATE; THIOESTER; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CYCLOADDITION; ONE POT SYNTHESIS; REACTION OPTIMIZATION; REACTION TIME; ROOM TEMPERATURE;

CHEMISTRY TECHNIQUES, SYNTHETIC; KINETICS; PYRIDINES; THIOPHENES;

EID: 80054117920     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200685e     Document Type: Article

References (50)

1. (a) Eicher, T.; Hauptmann, S.; Speicher, A. The Chemistry of Heterocycles; Wiley-VCH: New York, 2003; Chapter 5, Section 5.6.
2. (b) Russell, R. K.; Press, J. B. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. W. F., Padwa, A., Eds.; Pergamon; New York, 1996; Vol. 2, pp 679-729.
3. (c) Wu, C.; Decker, E. R.; Blok, N.; Bui, H.; You, T. J.; Wang, J.; Bourgoyne, A. R.; Knowles, V.; Berens, K. L.; Holland, G. W.; Brock, T. A.; Dixon, R. A. F. J. Med. Chem. 2004, 47, 1969-1986.
4. (a) Dore, K.; Dubus, S.; Ho, H. A.; Levesque, I.; Brunette, M.; Corbeil, G.; Boissinot, M.; Boivin, G.; Bergeron, M. G.; Boudreau, D.; Leclerc, M. J. Am. Chem. Soc. 2004, 126, 4240-4244.
5. (b) Pillai, A. D.; Rathod, P. D.; Xavier, F. P.; Vasu, K. K.; Padh, H.; Sudarsanam, V. Bioorg. Med. Chem. 2004, 12, 4667-4671.
6. (c) Ramos, A. C.; Pelaez, R.; Lopez, J. L.; Caballero, E.; Medarde, M.; San Feliciano, A. Tetrahedron 2001, 57, 3963-3977.
7. (a) Rassu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Chem. Soc. Rev. 2000, 29, 109-118.
8. (b) Yu, H.; Pullen, A. E.; Buschel, M. G.; Swager, T. M. Angew. Chem., Int. Ed. 2004, 43, 3700-3703.
9. Zeybek, H. Turk Veteriner Hekimleri Dernegi Dergisi 1970, 40, 11-17.
10. Bristol-Myers Squibb. http://www.bms.com.
11. Schulze, K. E.; Cohen, P. R.; Nelson, B. R. Dermatol. Surg. 2006, 32, 407-410.
12. McMurry, T. B. H. DNA Repair 2007, 6, 1161-1169.
13. Dolman, N. P.; More, J. C. A.; Alt, A.; Knauss, J. L.; Pentikainen, O. T.; Glasser, C. R.; Bleakman, D.; Mayer, M. L.; Collingridge, G. L.; Jane, D. E. J. Med. Chem. 2007, 50, 1558-1570.
14. Muccini, M. Nat. Mater. 2006, 5, 605-613.
15. Mishra, A.; Ma, C.-Q.; Bauerle, P. Chem. Rev. 2009, 109, 1141-1276.
16. Noda, T.; Ogawa, H.; Noma, N.; Shirota, Y. Adv. Mater. 1997, 9, 720-722.
17. (a) Ortiz, R. P.; Casado, J.; Hernandez, V.; Lopez Navarrete, J. T.; Letizia, J. A.; Ratner, M. A.; Facchetti, A.; Marks, T. J. Chem. - Eur. J. 2009, 15, 5023-5039.
18. (b) Ong, B. S.; Wu, Y.; Li, Y.; Liu, P.; Pan, H. Chem. - Eur. J. 2008, 14, 4766-4778.
19. Dario, P.; Marco, A.; Giuseppe, G.; Roberto, C.; Margherita, Z.-R.; Guglielmo, L.; Giovanna, B.; Laura, F. Appl. Phys. Lett. 2002, 81, 3534-3536.
20. (a) Zen, A.; Bilge, A.; Galbrecht, F.; Alle, R.; Meerholz, K.; Grenzer, J.; Neher, D.; Scherf, U.; Farrell, T. J. Am. Chem. Soc. 2006, 128, 3914-3915.
21. (b) Ma, C.-Q.; Mena-Osteritz, E.; Debaerdemaeker, T.; Weink, M. M.; Janssen, R. A. J.; Bauerle, P. Angew. Chem., Int. Ed. 2007, 46, 1679-1683.
22. (a) Ie, Y.; Umemoto, Y.; Okabe, M.; Kusunoki, T.; Nakayama, K. I.; Pu, Y. J.; Kido, J.; Tada, H.; Aso, Y. Org. Lett. 2008, 10, 833-836.
23. (b) Ie, Y.; Nitani, M.; Ishikawa, M.; Nakayama, K. I.; Tada, H.; Kaneda, T.; Aso, Y. Org. Lett. 2007, 9, 2115-2118.
24. (a) Roncali, J. Chem. Rev. 1997, 97, 173-205.
25. (b) Moghaddam, F. M.; Boinee, H. Z. Tetrahedron 2004, 60, 6085-6089.
26. (c) Minetto, G.; Raveglia, L. F.; Sega, A.; Taddei, M. Eur. J. Org. Chem. 2005, 5277-5288.
27. (d) Kaleta, Z.; Makowski, B. T.; Soos, T.; Dembinski, R. Org. Lett. 2006, 8, 1625-1628.
28. (e) Nakamura, I.; Sato, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2006, 45, 4473-4475.
29. (a) Gewald, K. Angew. Chem. 1961, 73, 114-118.
30. (b) Campaigne, E.; Foye, W. O. J. Org. Chem. 1952, 62, 1405-1412 and references therein.
31. (a) Gronowitz, S. The Chemistry of Heterocyclic Compounds: Thiophene and its Derivatives; Gronowitz, S. J.; Ed.; Wiley and Sons: New York, 1991; Vol. 44, Part 3, Chapter 2.
32. (b) Okazawa, T.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2002, 124, 5286-5287.
33. (a) Gabriele, B.; Salerno, G.; Fazio, A. Org. Lett. 2000, 2, 351-352.
34. (b) Fazio, A.; Gabriele, B.; Salerno, G.; Destri, S. Tetrahedron 1999, 55, 485-502.
35. (c) Wang, M.; Ai, L.; Zhang, J.; Liu, Q.; Gao, L. Chin. J. Chem. 2002, 20, 1591-1597.
36. (a) Sommen, G.; Comel, A.; Kirsch, G. Synthesis 2004, 451-455.
37. (b) Thomae, D.; Kirsch, G.; Seck, P. Synthesis 2007, 1027-1032.
38. (a) Sun, J.; Wu, Q.; Xia, E.-Y.; Yan, C.-G. Synthesis 2010, 3987-3992.
39. (b) O' Connor, C. J.; Roydhouse, M. D.; Przybyt, A. M.; Wall, M. D.; Southern, J. M. J. Org. Chem. 2010, 75, 2534-2538.
40. (c) Jalani, H. B.; Kaila, J. C.; Baraiya, A. B.; Pandya, A. N.; Sudarsanam, V.; Vasu, K. K. Tetrahedron Lett. 2010, 51, 5686-5689.
41. Samuel, R.; Chandran, P.; Retnamma, S.; Sasikala, K. A.; Sreedevi, N. K.; Anabha, E. R.; Asokan, C. V. Tetrahedron 2008, 64, 5944-5948.
42. Lee, H. S.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2009, 50, 6480-6483 and references therein.
43. Samuel, R.; Asokan, C. V.; Suma, S.; Chandran, P.; Retnamma, S.; Anabha, E. R. Tetrahedron Lett. 2007, 48, 8376-8378.
44. (a) Singh, O. M.; Devi, N. S.; Thokchom, D. S.; Sharma, G. J. Eur. J. Med. Chem. 2010, 45, 2250-2257.
45. (b) Singh, O. M.; Devi, N. S. J. Org. Chem. 2009, 74, 3141-3144.
46. (a) Nandi, G. C.; Samai, S.; Singh, M. S. J. Org. Chem. 2010, 75, 7785-7795.
47. (b) Verma, R. K.; Verma, G. K.; Raghuvanshi, K.; Singh, M. S. Tetrahedron 2011, 67, 584-589.
48. (c) Chowdhury, S.; Nandi, G. C.; Samai, S.; Singh, M. S. Org. Lett. 2011, 13, 3762-3765.
49. Wurz, R. P. Chem. Rev. 2007, 107, 5570-5595.
50. The crystallographic coordinates have been deposited with the Cambridge Crystallographic Data Centre; deposition no. CCDC 818986 (3b). These data can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Rd., Cambridge CB2 1EZ, UK or via www.ccdc.cam.ac.uk/conts/retrieving. html.